Helical chirality of poly(quinoxaline-2,3-diyl)s bearing a boronyl pendant at the 5-position of the quinoxaline ring was induced by condensation with chiral guests such as a diol, diamine, and amino alcohol. Reversible induction of a single-handed helical structure was achieved by using less than an equimolar amount of chiral amino alcohols to the boronyl pendants. Majority-rule-effect-based chiral amplification on the polyquinoxaline main chain was demonstrated with chiral amino alcohols with low enantiomeric excess (ee). The helical macromolecular scaffold whose helicity was thus induced was utilized in palladium-catalyzed asymmetric silaboration of meso-methylenecyclopropane (up to 92% ee) by introducing (diarylphosphino)phenyl pendants at their side chains.